The Work Continues: Notes for the Seasoned Leader

Dear Long-Time Executive Director,

After years of serving as a leader, you have seen a lot: budget cycles, board transitions, staff changes, shifting community expectations, a pandemic, probably a weather-related disaster, a fiscal crisis, and many 3 a.m. wake-ups when you're mentally writing a speech or preparing for the next day, and probably the anxiety of worrying about whether you'll make payroll on Friday. Even if you’ve been in your leadership role for many years, it’s helpful to remember what it felt like at the start (less the newbie social butterflies)—and to stay focused on what still needs your attention. Here are a few thoughts:

Strategic planning remains part of your role.
Even if you’ve been through several rounds of planning over the years, it’s important to keep the process active and relevant. A plan isn't any good if it's on the shelf or in the cloud. The plan needs to be living and referred to often. Set aside regular time to reflect on your organization’s direction and reset where needed. If your current plan hasn’t been referred to in a while, ask why. Don't be afraid to dust it off on your own—rewrite it based on what you, as the expert, know about your organization. Then, bring together senior staff, board leadership, and perhaps a donor or community partner to take a look at what you've done. You may have saved the organization a lot of time and money by taking the reins on your own. Regardless of how you get it done, make sure you have a strategic plan and the framework for an implementation and measurement plan. It's essential to maintain clarity about where you're headed and how you’ll get there (or you won't).

Maintain a current list of people who have been especially important to the organization’s success—and stay in touch with them.
This might include donors, former board members, alumni of your programs, long-time volunteers, community leaders, and staff members who carry institutional knowledge. This for sure should include any elected or appointed government officials who represent your district, or who are passionate about your cause (even if they represent a district across the country). These individuals must not be simply names in a database—they are people who care about your mission and/or your organization. It’s worth reaching out when you don’t have an immediate ask, and always send a sincere note of thanks if they engage with you. And even if they don't respond, you'll know you tried.

Even though they are officially in charge, it's your job to lead your board.
They rely on your clarity and want you to lead—that's why they hired you and keep you around! When asking for their input or requesting they make a decision, try to be specific in what you’re seeking. If you open a discussion, be ready to engage with the ideas that come forward—or be prepared for quiet. When offering recommendations, bring the necessary context and financial implications. Help them stay focused on what matters most: governance, strategic direction, and their broader role as ambassadors for the mission. One great way to do that is to really understand each board member's specific area of expertise and ask them for their advice in that area. They will feel more engaged in your organization and committed to you as its leader.

Succession planning is part of your responsibility.
Even if there’s no immediate transition on the horizon, it’s wise to plan ahead for both staff and board succession. That includes building a strong team, documenting key processes, and talking openly with your teams about leadership continuity, including contingent and planned succession planning. Your next board leader or executive leader might already be part of your organization—and making space for that possibility can help set in place professional development opportunities and ensure a smoother future.

Support your staff by offering both clarity and protection.
One of your key roles is to make it easier for others to do their best work. Share your vision, but don’t overwhelm people with every detail. Pay attention to your own energy—if you’re feeling anxious, your team probably is too. Lead with steadiness and an open mind. Celebrate accomplishments regularly, and give credit generously.

Advocacy matters a lot.
Direct service alone doesn’t resolve the challenges your organization is working to address. Part of your role is to help others—board members, partners, and policymakers—understand the broader context in which your mission operates. Whether through education, coalition-building, legislative action, or public engagement, your leadership can help strengthen awareness and impact.

Take time to review potential risks.
The longer you’ve been in your role, the easier it is to become accustomed to slow-moving vulnerabilities. That’s often when they become real. Revisit your enterprise risk management plan and emergency protocols each year. Refresh your communications plan, your contact lists, do table-top exercises when you role-play scenarios of who takes the lead in different crises. Get to know your local emergency personnel. Ensure your phone tree (remember those!) is up to date; preparation goes a long way in times of pressure. And this is a big one: consider whether now is the time to enter into a strategic partnership or even merge with another organization with a mission similar to or adjacent to yours. This takes guts and a lot of initiative, but can be effective in helping to achieve impact.

You don’t need to do everything from scratch.
There are strong templates and shared practices across the nonprofit field—use them. Lean on your peers, consult experts and software when needed, and consider what’s already working well elsewhere. There’s no extra credit for reinventing the wheel!

You've come this far.
Consistency, especially in the face of change and uncertainty, is a quiet and powerful form of leadership. Coupled with vision, strategic planning, succession planning, and always seeking to uncover your own and your organization's blindspots is a powerful way to stay fresh in the role and there for those who rely on you and your organization.

We’re in this together,
Sophia